An improved pictet-spengler condensation: A convenient synthetic route to bioactive manzamine derivatives

Heterocycles

Volumn 71, Issue 2, 2007, Pages 245-252

  Choo, Yeun Mun ^a   Hamann, Mark T ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547109132     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-10937     Document Type: Article

References (32)

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17. 2 (3 mL) for 2 h. TFA (50 μL) was then added to the reaction mixture and further stirred for another 3 h at 50°C. The reaction mixture was chromatographed over silica gel immediately to give manzamine D (7a, 52.7 mg, 86%).
18. 2 (3 mL) for 2 h. TFA (50 μL) was then added to the reaction mixture and further stirred for another 3 h at 50°C. The reaction mixture was chromatographed over silica gel immediately to give the Pictet-Spengler product (4, 104.1 mg, 75%).
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22. 4O + H).
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28. 4O + H).
29. Ircinal A (1, 50.9 mg) and tryptamine (3, 30.8 mg) in 1 mL anhydrous EtOH were added to 0.2 mL of TFA. The mixture was then absorded onto 1.5 g of silica gel. The silica mixture was placed in a glass vessel and was irradiated in a microwave oven (Panasonic NN-S543BFR-1300W) at 390 W for 10 min. The crude mixture was then eluted from the silica gel using acetone, concentrated, and chromatographed over silica gel to furnish manzamine D (7a, 15.3 mg, 23 %), epi-manzamine D (7b, 12.6 mg, 19%), and unreacted ircinal A (1, 16.3 mg).
30. 4), and evaporated to give brownish oil. Chromatography of the crude over silica gel afforded manzamine A (12, 5.6 mg, 50 %) and unreacted manzamine D (7a, 5.1 mg, 50%). The 1H NMR and ESI-MS data of 12 were identical with the reported data of manzamine A (ref. 1).
31. 2 + H).
32. 3 + H).